Sulfuric Acid → HCID 22225351, compound

HRID 1744806Notes

Reaction equation

HRID 1744806 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:37]=[CH:36][C:9]([NH:10][C:11]2[N:12]=[C:13]([CH3:35])[C:14]3[CH:20]=[CH:19][C:18](=[O:21])[N:17]([C:22]4[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29](C)(C)C)=[O:27])=[CH:24][CH:23]=4)[C:15]=3[N:16]=2)=[CH:8][CH:7]=1)=[O:5])C.OS(O)(=O)=O>CO>[CH3:29][O:28][C:26]([C:25]1[CH:33]=[CH:34][C:22]([N:17]2[C:15]3[N:16]=[C:11]([NH:10][C:9]4[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:1])=[O:5])=[CH:37][CH:36]=4)[N:12]=[C:13]([CH3:35])[C:14]=3[CH:20]=[CH:19][C:18]2=[O:21])=[CH:23][CH:24]=1)=[O:27]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22225233HCID 22225233, compound

Product 1

HCID 22225351HCID 22225351, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 3 (0.100 g; 0.200 mmol) and 96% H2SO4 (1 mL) in 100 mL of methanol was stirred under reflux for 24 h. The reaction mixture was concentrated, diluted with methylene chloride, and washed with aqueous sodium bicarbonate. The organic phase was dried over anhydrous sodium sulphate, concentrated and purified by silica gel column chromatography (eluant: CH2Cl2/CH3OH=190/10) to yield compound 41 (0.05 g; 56%).

Workup

  1. temperatureunder reflux for 24 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with methylene chloride
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (eluant: CH2Cl2/CH3OH=190/10)

Sources & evidence

ORD record
ord-d45f0f39f97844de9e794c1c8a969152
Source dataset
uspto-grants-2006_03
Patent number
US07019002B2

Reaction notes

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